Sodium Hydroxide → 5-{4-[(Tert-butoxy)carbonyl]piperazin-1-yl}thiophene-2-carboxylic acid

HRID 1911316

Reaktionsgleichung

Reaktionsgleichung von HRID 1911316
[CH:1]([C:3]1[S:7][C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:5][CH:4]=1)=[O:2].[OH-:21].[Na+]>C(O)C.O.[N+]([O-])([O-])=O.[Ag+]>[CH3:18][C:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][N:8]([C:6]2[S:7][C:3]([C:1]([OH:21])=[O:2])=[CH:4][CH:5]=2)[CH2:9][CH2:10]1)=[O:15])([CH3:20])[CH3:19]

Komponenten

6

Edukt 2

HCID 14798Sodium HydroxideHCID 28065298Tert-butyl 4-(5-formylthiophen-2-yl)piperazine-1-carboxylate

Produkt 1

HCID 543134535-{4-[(Tert-butoxy)carbonyl]piperazin-1-yl}thiophene-2-carboxylic acidAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24470Silver NitrateKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A solution of tert-butyl 4-(5-formylthien-2-yl)piperazine-1-carboxylate (2.51 g, 8.50 mmol) in ethanol (85 ml) was added in one portion to a solution of silver (I) nitrate (10.0 g, 58.8 mmol) and sodium hydroxide (4.83 g, 120.6 mmol) in water (85 ml). This mixture was stirred and heated at 65° C. for 22 h. The mixture was cooled by the addition of ice and then filtered to remove silver salts. The filtrate was carefully evaporated to remove the ethanol and the resulting aqueous solution was filtered again through a glass-fibre pad to remove tarry material. The filtrate was then diluted with water to a total volume of 400 ml and then acidified to pH 5 with acetic acid. The precipitate was filtered off, washed with water and then dried in a vacuum oven at 45° C. overnight to give 5-[4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]thiophene-2-carboxylic acid (1.88 g, 71%).

Aufarbeitung

  1. temperatureThe mixture was cooled by the addition of ice
  2. filtrationfiltered
  3. customto remove silver salts
  4. customThe filtrate was carefully evaporated
  5. customto remove the ethanol
  6. filtrationthe resulting aqueous solution was filtered again through a glass-fibre pad
  7. customto remove tarry material
  8. additionThe filtrate was then diluted with water to a total volume of 400 ml
  9. filtrationThe precipitate was filtered off
  10. washwashed with water
  11. customdried in a vacuum oven at 45° C. overnight

Quellen und Nachweise

ORD-Eintrag
ord-5d15b5d95073431c8f20077d38fdb5ca
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604022B2

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